Inman Connect Las Vegas returns live, Oct. 26-28, 2021, at the Aria Hotel and Resort in Las Vegas, Nevada. In the lead-up to the big event, we’re talking with scheduled speakers about the moments that made their careers. Consider this just a taste of all the knowledge that will be shared at ICLV. Make plans to join us.
Move Inc. has been having a good year.
After a slump in 2020, the company — which operates realtor.com and is owned by News Corp. — revealed in August that it recently saw its revenue rebound 30 percent to nearly $2.5 billion.
Presiding over this change in Move’s fortunes is CEO David Doctorow, a former executive from eBay and Expedia who has been running the real estate tech firm for nearly two years now. Doctorow has in the past been vocal about his belief that real estate needs to become easier for consumers. And while at Move he has made key decisions related to staffing, acquisitions and the company’s offerings that highlight a proactive vision of the company’s future.
Next month, Doctorow will appear at Inman Connect Las Vegas. In the lead up to that event, he recently sat down with Inman to discuss three key moments that turned him into the leader he is today.
A childhood in Paris
When Doctorow was 7 years old, his dad got a job that required the family to move to Paris. They stayed for about two years, during which time Doctorow and his parents traveled to most of western Europe. It was an eye-opening period.
“It was this experience over those couple of years, of visiting different places, going to an international school with students from 50 different countries, that taught me something about culture and empathy,” Doctorow said.
He went on to recall his first encounter with snails as food. The young Doctorow was in a Parisian restaurant that has operated for centuries, and both his dad and the waiter mentioned that the common garden pest was actually on the menu.
“My first reaction was like, what? Why would anyone want to eat that?” Doctorow recalled.
After the initial shock wore off, though, Doctorow decided to take a chance and try escargot. And to his own surprise, he liked it. The experience has stuck with him to this day, and he said it continues to serve as a reminder to stay curious and to be open to new things.
“It was a very memorable experience to realize that something, coming in, I would have thought would be disgusting actually was incredibly delicious,” he explained. “It was an analog to what happened as I got exposed to the world over those years.”
Doctorow said his time in Europe as a child ultimately helped him adopt a leadership style that prioritizes empathy, curiosity and humility.
“This experience in my childhood really does carry through to today in an appreciation of organizational culture,” he said.
A teenage leadership camp
As a teenager, Doctorow joined his high school marching band. By the time his junior year was rolling around, he had risen to become drum major — the band’s leader.
But despite the role, and the fact that he had strong leadership role models in his life, Doctorow said he didn’t necessarily conceive of himself as a leader when he was a teenager.
However, the summer before his junior year began, his role as drum major allowed him to attend a week-long leadership camp. It proved to be a life-changing experience.
“It went from being a title, being a leader, to being something very deeply personal for me, which was much more about a mindset and an approach rather than a title,” he recalled.
Doctorow described the camp as a “crash course” in leadership best practices, and it was an early instance during which he began to think critically about skills such as listening and challenging the people around him. He learned about how to keep people engaged, and how to ask questions.
It was a brief moment, but Doctorow soon got to put his new skills to the test.
“I got so excited to just keep learning more about how one becomes a leader,” Doctorow said. “And then I went back to my band and was able to begin leading these rehearsals. I really fell in love, in this period of time, with the idea that as a leader you could really make a difference to the people around you.”
Obviously, Doctorow has gone on to have much more leadership experience and training over the years. But this early moment acted as a kind of spark, and helped set him on a course that would see him in top roles at many big-name companies — including Move.
“Boy am I grateful for that moment,” he added of the camp. “It changed me forever.”
A key mentor
In 2011, many years after his Paris and drum major years, Doctorow ended up working as the chief marketing and strategy officer for Expedia. He stayed at the travel company for about five years, and during that tenure he worked under then-CEO Dara Khosrowshahi, who now leads Uber.
“That five-year experience of working side-by-side with him, him coaching me and me watching him, has shaped me into the leader I am now,” Doctorow said.
Doctorow praised Khosrowshahi for being able to see both the big picture of what was going on in the company, as well as small issues that needed to be addressed. Khosrowshahi was consistently approachable and, as one might expect for a web-based company like Expedia, “ultimately tended to solve problems by putting technology at the center,” Doctorow recalled.
Doctorow went on to point to a number of Move’s recent successes. Web traffic has grown to historic levels, he noted, while realtor.com is outpacing rivals and hitting new revenue highs. Doctorow said the company has ultimately become more disciplined, and is focusing on doing fewer things really well. And he connected these many successes to leadership lessons he learned at Expedia.
“I point back to my experience working with Dara [Khosrowshahi],” Doctorow said, adding that he still considers his former boss a friend and mentor.
Despite his long resumé, Doctorow said that professionally he’s still “just getting started.” But in the end, he also noted that his experience with Khosrowshahi captured a recurring theme among the most pivotal moments in his life.
“I think in a way what I draw out as a theme among these three moments,” Doctorow concluded, “is this underlying desire to learn and keep improving.”
